HRP20220621T1 - Postupak sinteze za proizvodnju (s)-(2r,3r,11br)-3-izobutil-9,10-dimetoksi-2,3,4,6,7,11b-heksahidro-1h-pirido[2,1-a]izokinolin-2-il 2-amino-3-metilbutanoat di(4-metilbenzensulfonata) - Google Patents
Postupak sinteze za proizvodnju (s)-(2r,3r,11br)-3-izobutil-9,10-dimetoksi-2,3,4,6,7,11b-heksahidro-1h-pirido[2,1-a]izokinolin-2-il 2-amino-3-metilbutanoat di(4-metilbenzensulfonata) Download PDFInfo
- Publication number
- HRP20220621T1 HRP20220621T1 HRP20220621TT HRP20220621T HRP20220621T1 HR P20220621 T1 HRP20220621 T1 HR P20220621T1 HR P20220621T T HRP20220621T T HR P20220621TT HR P20220621 T HRP20220621 T HR P20220621T HR P20220621 T1 HRP20220621 T1 HR P20220621T1
- Authority
- HR
- Croatia
- Prior art keywords
- dimethoxy
- pyrido
- isobutyl
- hexahydro
- amino
- Prior art date
Links
- FOWYYVFZQZDXAO-UHFFFAOYSA-N CC1=CC=C(C=C1)S(=O)(=O)O.CC1=CC=C(C=C1)S(=O)(=O)O.NC(C(=O)O)C(C)C Chemical compound CC1=CC=C(C=C1)S(=O)(=O)O.CC1=CC=C(C=C1)S(=O)(=O)O.NC(C(=O)O)C(C)C FOWYYVFZQZDXAO-UHFFFAOYSA-N 0.000 title claims 11
- 238000002360 preparation method Methods 0.000 title 1
- 238000010189 synthetic method Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 47
- 238000006243 chemical reaction Methods 0.000 claims 33
- 150000003839 salts Chemical class 0.000 claims 21
- 239000002904 solvent Substances 0.000 claims 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 18
- WEQLWGNDNRARGE-UHFFFAOYSA-N b-Dihydrotetrabenazine Chemical compound C1CN2CC(CC(C)C)C(O)CC2C2=C1C=C(OC)C(OC)=C2 WEQLWGNDNRARGE-UHFFFAOYSA-N 0.000 claims 18
- NECCWFYTRPJLPE-UHFFFAOYSA-N 2-amino-3-methylbutanoic acid dihydrochloride Chemical compound Cl.Cl.NC(C(=O)O)C(C)C NECCWFYTRPJLPE-UHFFFAOYSA-N 0.000 claims 14
- 239000002253 acid Substances 0.000 claims 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 12
- TXYMVANDPQOMEU-DNRBGDKYSA-N [(2R,3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl] (2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate Chemical compound C(C)(C)(C)OC(=O)N[C@H](C(=O)O[C@@H]1C[C@H]2N(CCC3=CC(=C(C=C23)OC)OC)C[C@H]1CC(C)C)C(C)C TXYMVANDPQOMEU-DNRBGDKYSA-N 0.000 claims 11
- 239000012453 solvate Substances 0.000 claims 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 8
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 7
- 230000015572 biosynthetic process Effects 0.000 claims 7
- NSLJVQUDZCZJLK-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydroisoquinoline Chemical compound C1CN=CC2=C1C=C(OC)C(OC)=C2 NSLJVQUDZCZJLK-UHFFFAOYSA-N 0.000 claims 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- 229940024606 amino acid Drugs 0.000 claims 6
- 150000001413 amino acids Chemical class 0.000 claims 6
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- QCDJYGZCMGEQNF-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-5-methylhexan-2-one Chemical compound CC(C)CC(C(C)=O)CN(C)C QCDJYGZCMGEQNF-UHFFFAOYSA-N 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 5
- MKJIEFSOBYUXJB-UHFFFAOYSA-N 9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2CC(CC(C)C)C(=O)CC2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-UHFFFAOYSA-N 0.000 claims 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 4
- 239000003638 chemical reducing agent Substances 0.000 claims 4
- 238000002425 crystallisation Methods 0.000 claims 4
- 230000008025 crystallization Effects 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 229960004295 valine Drugs 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical group CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 2
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 claims 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 2
- 239000002841 Lewis acid Substances 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 235000011054 acetic acid Nutrition 0.000 claims 2
- 150000001734 carboxylic acid salts Chemical class 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 2
- 238000010511 deprotection reaction Methods 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 2
- 239000012279 sodium borohydride Substances 0.000 claims 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 1
- BOWAADNPAIFJRC-XNNXXJIXSA-N (2R,3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-ol [(1S)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical class CC1(C)C2CC[C@@]1(CS(O)(=O)=O)C(=O)C2.COc1cc2CCN3C[C@@H](CC(C)C)[C@H](O)C[C@@H]3c2cc1OC BOWAADNPAIFJRC-XNNXXJIXSA-N 0.000 claims 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- PQXVEYYRJHMTEV-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydroisoquinolin-2-ium;chloride Chemical compound [Cl-].C1C[NH+]=CC2=C1C=C(OC)C(OC)=C2 PQXVEYYRJHMTEV-UHFFFAOYSA-N 0.000 claims 1
- AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 claims 1
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 239000012448 Lithium borohydride Substances 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- PMSGGBFTMLDQAW-TZYFFPFWSA-N [(2R,3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl] (2S)-2-amino-3-methylbutanoate dihydrochloride Chemical compound Cl.Cl.COc1cc2CCN3C[C@@H](CC(C)C)[C@@H](C[C@@H]3c2cc1OC)OC(=O)[C@@H](N)C(C)C PMSGGBFTMLDQAW-TZYFFPFWSA-N 0.000 claims 1
- MIOPJNTWMNEORI-OMNKOJBGSA-N [(4s)-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-OMNKOJBGSA-N 0.000 claims 1
- WGFIAYSNCVBBIH-GARYODESSA-N [C@]12(C(=O)CC(CC1)C2(C)C)CS(=O)(=O)O[C@@H]1C[C@H]2N(CCC3=CC(=C(C=C23)OC)OC)C[C@H]1CC(C)C Chemical group [C@]12(C(=O)CC(CC1)C2(C)C)CS(=O)(=O)O[C@@H]1C[C@H]2N(CCC3=CC(=C(C=C23)OC)OC)C[C@H]1CC(C)C WGFIAYSNCVBBIH-GARYODESSA-N 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- NQZKZGHOYUYCHU-UHFFFAOYSA-N boron;tetraethylazanium Chemical compound [B].CC[N+](CC)(CC)CC NQZKZGHOYUYCHU-UHFFFAOYSA-N 0.000 claims 1
- FLLNLJJKHKZKMB-UHFFFAOYSA-N boron;tetramethylazanium Chemical compound [B].C[N+](C)(C)C FLLNLJJKHKZKMB-UHFFFAOYSA-N 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 229960002510 mandelic acid Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562387442P | 2015-12-23 | 2015-12-23 | |
| EP16823529.9A EP3394057B1 (en) | 2015-12-23 | 2016-12-22 | Synthetic method for preparation of (s)-(2r,3r,11br)-3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1h-pyrido[2,1,-a]lsoquinolin-2-yl 2-amino-3-methylbutanoate di(4-methylbenzenesulfonate) |
| PCT/US2016/068277 WO2017112857A1 (en) | 2015-12-23 | 2016-12-22 | SYNTHETIC METHODS FOR PREPARATION OF (S)-(2R,3R,11BR)-3-ISOBUTYL-9,10-DIMETHOXY-2,3,4,6,7,11B-HEXAHYDRO-1H-PYRIDO[2,1,-A]lSOQUINOLIN-2-YL 2-AMINO-3-METHYLBUTANOATE DI(4-METHYLBENZENESULFONATE) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20220621T1 true HRP20220621T1 (hr) | 2022-06-24 |
Family
ID=57758848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20220621TT HRP20220621T1 (hr) | 2015-12-23 | 2016-12-22 | Postupak sinteze za proizvodnju (s)-(2r,3r,11br)-3-izobutil-9,10-dimetoksi-2,3,4,6,7,11b-heksahidro-1h-pirido[2,1-a]izokinolin-2-il 2-amino-3-metilbutanoat di(4-metilbenzensulfonata) |
Country Status (16)
| Country | Link |
|---|---|
| US (6) | US10160757B2 (ja) |
| EP (1) | EP3394057B1 (ja) |
| JP (3) | JP6869988B2 (ja) |
| CN (1) | CN108925135A (ja) |
| CA (1) | CA3009169A1 (ja) |
| DK (1) | DK3394057T3 (ja) |
| ES (1) | ES2911351T3 (ja) |
| HR (1) | HRP20220621T1 (ja) |
| HU (1) | HUE059065T2 (ja) |
| LT (1) | LT3394057T (ja) |
| MA (1) | MA44127A (ja) |
| PL (1) | PL3394057T3 (ja) |
| PT (1) | PT3394057T (ja) |
| RS (1) | RS63170B1 (ja) |
| SI (1) | SI3394057T1 (ja) |
| WO (1) | WO2017112857A1 (ja) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2972600T3 (es) | 2015-10-30 | 2024-06-13 | Neurocrine Biosciences Inc | Sales de diclorhidrato de valbenazina y polimorfos de las mismas |
| EP3394057B1 (en) | 2015-12-23 | 2022-03-30 | Neurocrine Biosciences, Inc. | Synthetic method for preparation of (s)-(2r,3r,11br)-3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1h-pyrido[2,1,-a]lsoquinolin-2-yl 2-amino-3-methylbutanoate di(4-methylbenzenesulfonate) |
| US11242341B2 (en) | 2016-10-06 | 2022-02-08 | Assia Chemical Industries Ltd. | Solid state forms of valbenazine |
| EP3568394A1 (en) | 2017-01-10 | 2019-11-20 | Sandoz AG | Crystalline valbenazine free base |
| CN110769826A (zh) | 2017-01-27 | 2020-02-07 | 纽罗克里生物科学有限公司 | 施用某些vmat2抑制剂的方法 |
| US10954235B2 (en) * | 2017-02-27 | 2021-03-23 | Sandoz Ag | Crystalline forms of valbenazine salts |
| GB201705303D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705304D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705302D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705306D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| MA50175A (fr) | 2017-09-21 | 2021-04-21 | Neurocrine Biosciences Inc | Formulation de valbenazine à dosage élevé et compositions, procédés et kits associés |
| US10993941B2 (en) | 2017-10-10 | 2021-05-04 | Neurocrine Biosciences, Inc. | Methods for the administration of certain VMAT2 inhibitors |
| CN111836543A (zh) | 2017-10-10 | 2020-10-27 | 纽罗克里生物科学有限公司 | 施用某些vmat2抑制剂的方法 |
| KR20200108828A (ko) | 2017-11-22 | 2020-09-21 | 아시아 케미컬 인더스트리스 리미티드 | 발베나진의 고상 형태 |
| CN110621674B (zh) * | 2017-12-26 | 2022-03-29 | 苏州科睿思制药有限公司 | 一种Valbenazine二对甲苯磺酸盐的晶型及其制备方法和用途 |
| AU2019322863A1 (en) | 2018-08-15 | 2021-03-11 | Neurocrine Biosciences, Inc. | Methods for the administration of certain VMAT2 inhibitors |
| CA3065236A1 (en) | 2018-12-27 | 2020-06-27 | Apotex Inc. | Novel crystalline form of valbenazine dibesylate |
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| ES2911351T3 (es) | 2022-05-18 |
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| US10160757B2 (en) | 2018-12-25 |
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| US20200347057A1 (en) | 2020-11-05 |
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| JP6869988B2 (ja) | 2021-05-12 |
| US10906903B2 (en) | 2021-02-02 |
| CA3009169A1 (en) | 2017-06-29 |
| CN108925135A (zh) | 2018-11-30 |
| US20200347056A1 (en) | 2020-11-05 |
| JP2021046454A (ja) | 2021-03-25 |
| US20200347054A1 (en) | 2020-11-05 |
| DK3394057T3 (da) | 2022-04-11 |
| US10919892B2 (en) | 2021-02-16 |
| PT3394057T (pt) | 2022-04-21 |
| EP3394057A1 (en) | 2018-10-31 |
| LT3394057T (lt) | 2022-06-27 |
| US20170183346A1 (en) | 2017-06-29 |
| PL3394057T3 (pl) | 2022-08-22 |
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